(1S)-homonopol | 144606-02-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S)-homonopol
• 英文别名: homonopol；(-)-(1R)-6,6-Dimethylbicyclo<3.1.1>hept-2-ene-2-propanol；3-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)propan-1-ol；3-[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]propan-1-ol
• CAS: 144606-02-0
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: LKERPLDCSYHOIC-QWRGUYRKSA-N

物化性质

• 沸点：
  265.8±19.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S)-homonopol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.25h， 生成 7-(3-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)propoxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Monoterpene-Containing Substituted Coumarins as Inhibitors of Respiratory Syncytial Virus (RSV) Replication

  摘要：

  呼吸道合胞病毒（RSV）是婴儿死亡的一个重要原因。然而，目前尚无疫苗和足够的药物用于治疗。我们首次展示，O-连接的香豆素-单萜共轭物是有效的RSV抑制剂。最有效的化合物对RSV的A型和B型两种血清型都具有活性。根据添加时间实验的结果，这些共轭物在病毒周期的早期阶段起作用。根据分子模拟数据，RSV F蛋白可能被视为一个可能的靶点。

  DOI：

  10.3390/molecules26247493
• 作为产物：
  描述：

  (1R)6,6-二甲基联环(3.1.1)庚烷-2-烯-2-乙醇 在 吡啶 、 碘 、 magnesium 、 sodium bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 26.0h， 生成 (1S)-homonopol
  参考文献：
  名称：

  Asymmetric reductions of prochiral ketones with lithium [2-[2-benzyloxy)ethyl]-6,6-dimethylbicyclo[3.1.1]-3-nonyl]-9-boratabicyclo-[3.3.1]nonane (lithium NB-Enantride) and its derivatives

  摘要：

  NB-Enantride, prepared by hydroboration of nopyl benzyl ether with 9-borabicyclo[3.3.1]nonane (9-BBN) followed by treatment with tert-butyllithium, is an effective asymmetric reducing agent. Especially noteworthy is the fact that it can reduce aliphatic ketones such as 2-octanone or 2-butanone in efficiencies approaching 80% enantiomeric excess. Several analogues have been tested in order to probe the structural features which contribute to making this reagent effective. The ether group evidently plays a role in obtaining high selectivity, since changing oxygen to nitrogen or sulfur causes a drop in selectivity. Moving the ether group by one atom in either direction or making it more hindered causes a drop in selectivity. However, replacing the OCH2C6H5 group with a methyl group also results in an effective reducing agent and suggests that steric factors play an important role. The lithium cation was also found to be very important. Whereas the lithium compound reduced acetophenone within minutes at -78-degrees-C, the potassium analogue gave no reduction over an extended period. At higher temperatures (-65-degrees-C) reduction did slowly occur with the potassium compound, but the selectivity was greatly reduced in comparison to the lithium compound.

  DOI：

  10.1021/jo00003a030

文献信息

• Matteson Reaction under Flow Conditions: Iterative Homologations of Terpenes
  作者：Conrad Kuhwald、Andreas Kirschning

  DOI：10.1021/acs.orglett.1c01222

  日期：2021.6.4

  The Matteson reaction is ideally suited for flow chemistry since it allows iterative homologation of boronate esters. The present study provides accurate data on reaction times of the individual steps of the Matteson reaction, which occurs in less than 10 s in total. The protocol allows terpenes to be (per-)homologated in a controlled manner to yield homo-, bishomo-, and trishomo-terpenols after oxidative

  Matteson 反应非常适合流动化学，因为它允许硼酸酯的迭代同系化。本研究提供了有关马特森反应各个步骤的反应时间的准确数据，该反应总共发生在 10 秒以内。该协议允许萜烯以受控方式进行 (per-) homologated, 以在氧化处理后产生 homo-、bishomo-和 trishomo-terpenols。新萜醇的嗅觉特性得到验证。
• Preparation of Campholenal Analogues: Chirons for the lipophilic moiety of sandalwood-like odorant alcohols
  作者：Christian Chapuis、Robert Brauchli

  DOI：10.1002/hlca.19920750507

  日期：1992.8.13

  In connection with structure-activity relationship studies, analogues of campholenal ((+)-4b), an important building block for sandalwood-like odorants, were prepared. The five-membered-ring analogues 4 were obtained by epoxidation of the corresponding α-pinene derivatives 2, followed by catalytic ZnBr2 isomerisation (Scheme 2). The six-membered-ring skeleton was obtained by ozonolysis of α-campholenyl

  结合结构-活性关系研究，制备了樟脑类似物（（+）- 4b），它是檀香状增香剂的重要组成部分。通过将相应的α- by烯衍生物2环氧化，然后进行催化的ZnBr 2异构化（流程2），获得五元环类似物4。通过臭氧分解α-樟脑烯基乙酸酯（（-）- 14b），然后进行分子内羟醛缩合，获得六元环骨架（方案5）。给出13 C-NMR分配。
• New Inhibitors of Respiratory Syncytial Virus (RSV) Replication Based on Monoterpene-Substituted Arylcoumarins
  作者：Tatyana M. Khomenko、Anna A. Shtro、Anastasia V. Galochkina、Yulia V. Nikolaeva、Anzhelika V. Garshinina、Sophia S. Borisevich、Dina V. Korchagina、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.3390/molecules28062673

  日期：——

  Respiratory syncytial virus (RSV) causes annual epidemics of respiratory infection. Usually harmless to adults, the RSV infection can be dangerous to children under 3 years of age and elderly people over 65 years of age, often causing serious problems, even death. At present, there are no vaccines and specific chemotherapeutic agents for the treatment of this disease, so the search for low-molecular weight compounds to combat RSV is a challenge. In this work, we have shown, for the first time, that monoterpene-substituted arylcoumarins are efficient RSV replication inhibitors at low micromolar concentrations. The most active compound has a selectivity index of about 200 and acts most effectively at the early stages of infection. The F protein of RSV is a potential target for these compounds, which is also confirmed by molecular docking and molecular dynamics simulation data.

  呼吸道合胞病毒（RSV）每年都会引起呼吸道感染流行。通常情况下，RSV 对成人无害，但对 3 岁以下儿童和 65 岁以上老人来说，RSV 感染可能很危险，往往会造成严重问题，甚至死亡。目前，还没有治疗这种疾病的疫苗和特异性化疗药物，因此寻找抗 RSV 的低分子量化合物是一项挑战。在这项研究中，我们首次发现单萜取代的芳基香豆素类化合物在低微摩尔浓度下是高效的 RSV 复制抑制剂。活性最高的化合物的选择性指数约为 200，在感染的早期阶段发挥最有效的作用。RSV 的 F 蛋白是这些化合物的潜在靶标，分子对接和分子动力学模拟数据也证实了这一点。
• Asymmetric reductions of prochiral ketones with lithium [2-[2-benzyloxy)ethyl]-6,6-dimethylbicyclo[3.1.1]-3-nonyl]-9-boratabicyclo-[3.3.1]nonane (lithium NB-Enantride) and its derivatives
  作者：M. Mark Midland、Aleksander Kazubski、Richard E. Woodling

  DOI：10.1021/jo00003a030

  日期：1991.2

  NB-Enantride, prepared by hydroboration of nopyl benzyl ether with 9-borabicyclo[3.3.1]nonane (9-BBN) followed by treatment with tert-butyllithium, is an effective asymmetric reducing agent. Especially noteworthy is the fact that it can reduce aliphatic ketones such as 2-octanone or 2-butanone in efficiencies approaching 80% enantiomeric excess. Several analogues have been tested in order to probe the structural features which contribute to making this reagent effective. The ether group evidently plays a role in obtaining high selectivity, since changing oxygen to nitrogen or sulfur causes a drop in selectivity. Moving the ether group by one atom in either direction or making it more hindered causes a drop in selectivity. However, replacing the OCH2C6H5 group with a methyl group also results in an effective reducing agent and suggests that steric factors play an important role. The lithium cation was also found to be very important. Whereas the lithium compound reduced acetophenone within minutes at -78-degrees-C, the potassium analogue gave no reduction over an extended period. At higher temperatures (-65-degrees-C) reduction did slowly occur with the potassium compound, but the selectivity was greatly reduced in comparison to the lithium compound.
• Synthesis and trichomonacidal activity of perketals and hydroperoxides
  作者：L. Cointeaux、J.-F. Berrien、B. Camuzat-Dedenis、V. Peyrou、O. Provot、C. Bories、P.M. Loiseau、J. Mayrargue

  DOI：10.1016/s0014-827x(02)01238-7

  日期：2002.5

  Some perketals were synthesized by the Dussault procedure using simple bromides and 2-methoxyprop-2-yl hydroperoxide. Treatment with acetic acid gave the corresponding hydroperoxides. Both perketals and hydroperoxides were tested in vitro as trichomonacidal agents. Most of them exhibited very good activities. Them most powerful compound was 2-methoxyprop-2-yl hexadec-1-yl peroxide which exhibited an IC50 value of 0.51 muM being 10 times more effective than the reference compound Metronidazole. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.